benzyl 2-((2-amino-3-carbamoylphenyl)carbamoyl)-3,4-dihydroquinoline-1(2H)-carboxylate → tert-butyl 2-(4-carbamoyl-1H-benzo[d]imidazol-2-yl)-3,4-dihydroquinoline-1(2H)-carboxylate

HRID 1895550Notes

Reaction equation

HRID 1895550 reaction equation
[NH2:1][C:2]1[C:7]([C:8](=[O:10])[NH2:9])=[CH:6][CH:5]=[CH:4][C:3]=1[NH:11][C:12]([CH:14]1[CH2:23][CH2:22][C:21]2[C:16](=[CH:17][CH:18]=[CH:19][CH:20]=2)[N:15]1[C:24]([O:26]CC1C=CC=CC=1)=[O:25])=O>C(O)(=O)C>[C:8]([C:7]1[C:2]2[N:1]=[C:12]([CH:14]3[CH2:23][CH2:22][C:21]4[C:16](=[CH:17][CH:18]=[CH:19][CH:20]=4)[N:15]3[C:24]([O:26][C:7]([CH3:8])([CH3:2])[CH3:6])=[O:25])[NH:11][C:3]=2[CH:4]=[CH:5][CH:6]=1)(=[O:10])[NH2:9]

Participants

3

Reactant 1

HCID 66889373benzyl 2-((2-amino-3-carbamoylphenyl)carbamoyl)-3,4-dihydroquinoline-1(2H)-carboxylate

Product 1

HCID 49854327tert-butyl 2-(4-carbamoyl-1H-benzo[d]imidazol-2-yl)-3,4-dihydroquinoline-1(2H)-carboxylate

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

Step-2: A solution of benzyl 2-((2-amino-3-carbamoylphenyl)carbamoyl)-3,4-dihydroquinoline-1(2H)-carboxylate (50 mg, 0.122 mmol) in acetic acid (2 ml) was heated to 80° C. and stirred for 2 h. The reaction mixture was concentrated, neutralized with aq. NaHCO3 and extracted with DCM. The DCM layer was washed with brine, dried over anhydrous sodium sulfate and evaporated. Purification of the crude product over preparative TLC using ethyl acetate/hexane mixture (2:1) as eluent afforded tert-butyl 2-(4-carbamoyl-1H-benzo[d]imidazol-2-yl)-3,4-dihydroquinoline-1(2H)-carboxylate. MS (ES+): m/z 393.23 [M+H]+

Workup

  1. concentrationThe reaction mixture was concentrated
  2. extractionextracted with DCM
  3. washThe DCM layer was washed with brine
  4. dry with materialdried over anhydrous sodium sulfate
  5. customevaporated
  6. customPurification of the crude product over preparative TLC

Sources & evidence

ORD record
ord-b94f0c354f7b4fb7be22a8097f6c9ea0
Source dataset
uspto-grants-2013_08
Patent number
US08513433B2

Reaction notes

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